Sodium Carbonate → HCID 136198175, compound

HRID 454588Notes

Reaction equation

HRID 454588 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.C(=O)(O)[O-].[Na+].C([O:17][C:18]1[CH:45]=[CH:44][C:43](B2OC(C)(C)C(C)(C)O2)=[CH:42][C:19]=1[C:20]([NH:22][C:23]1[CH:35]=[C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=[CH:32][C:24]=1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:21])(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.O.CO.COCCOC>[NH2:1][C:2]1[N:3]=[C:4]([C:43]2[CH:44]=[CH:45][C:18]([OH:17])=[C:19]([CH:42]=2)[C:20]([NH:22][C:23]2[CH:35]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:33]=[CH:32][C:24]=2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 3008092-Amino-6-bromopyridineHCID 516892Sodium BicarbonateHCID 66990469HCID 66990469, compound

Product 1

HCID 136198175HCID 136198175, compoundYield 46.3%

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Water (0.3 mL), 2-amino-6-bromopyridine (0.037 g), sodium bicarbonate (0.036 g), and bis(triphenylphosphine)palladium(II) dichloride (5.0 mg) were added to an ethylene glycol dimethyl ether (1 mL) suspension of tert-butyl 2-(2-acetoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)-4-phenylbenzoate (0.080 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then bis(triphenylphosphine)palladium(II) dichloride (5.0 mg) was added thereto, followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and methanol (0.3 mL) and sodium carbonate (0.046 g) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 20 minutes. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. The insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 90-60% hexane/ethyl acetate] to obtain 0.032 g of tert-butyl 2-(5-(6-aminopyridin-2-yl)-2-hydroxybenzamido)-4-phenylbenzoate.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 1 hour and 30 minutes
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 2 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. temperatureby heating
  7. temperatureto reflux under a nitrogen atmosphere for 20 minutes
  8. temperatureThe reaction mixture was cooled to room temperature
  9. customThe insoluble substance was removed by filtration
  10. customThe organic layer was separated
  11. washwashed with a saturated aqueous solution of sodium chloride
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe solvent was evaporated under reduced pressure
  14. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 90-60% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-0d494ae6cc1d44948e768151791c421b
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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